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Ligand-Promoted meta-C-H Amination and Alkynylation.

ABSTRACT: Using a modified norbornene (methyl bicyclo[2.2.1]hept-2-ene-2-carboxylate) as a transient mediator, meta-C-H amination and meta-C-H alkynylation of aniline and phenol substrates have been developed for the first time. Both the identification of a monoprotected 3-amino-2-hydroxypyridine/pyridone-type ligand and the use of a modified norbornene as a mediator are crucial for the realization of these two unprecedented meta-C-H transformations. A variety of substrates are compatible with both meta-C-H amination and meta-C-H alkynylation. Amination and alkynylation of heterocyclic substrates including indole, indoline, and indazole afford the desired products in moderate to high yields.

SUBMITTER: Wang P 

PROVIDER: S-EPMC5513786 | biostudies-literature | 2016 Oct

REPOSITORIES: biostudies-literature

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Ligand-Promoted meta-C-H Amination and Alkynylation.

Wang Peng P   Li Gen-Cheng GC   Jain Pankaj P   Farmer Marcus E ME   He Jian J   Shen Peng-Xiang PX   Yu Jin-Quan JQ  

Journal of the American Chemical Society 20161013 42

Using a modified norbornene (methyl bicyclo[2.2.1]hept-2-ene-2-carboxylate) as a transient mediator, meta-C-H amination and meta-C-H alkynylation of aniline and phenol substrates have been developed for the first time. Both the identification of a monoprotected 3-amino-2-hydroxypyridine/pyridone-type ligand and the use of a modified norbornene as a mediator are crucial for the realization of these two unprecedented meta-C-H transformations. A variety of substrates are compatible with both meta-C  ...[more]

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